tert-butyl 4-(4-(trifluoromethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate → Pyridine, 1,2,3,6-tetrahydro-4-[4-(trifluoromethyl)phenyl]-

Participants

Reaction Steps

A solution of 0.4 g (0.112 mmol) of 1-t-butoxycarbonyl-4-(4-trifluoromethyl phenyl)-1,2,3,6-tetrahydropyridine in 1 mL of TFA and 3 mL of CH2Cl2 was stirred at rt for 1 h. The reaction mixture was then concentrated. A mixture of the residue and 0.1 g of 10% Pd/C in 20 mL of MeOH was hydrogenated at 45 psi for 4 h. The reaction mixture was flitered though a plug of celite and concentrated to give 0.54 g of the title compound. 1H NMR (CDCl3) δ1.94 (m,2H), 2.06 (m, 2H), 3.00 (m, 1H), 3.11 (m, 2H), 3.49 (m, 2H), 7.45 (d, 2H, J=8 Hz), 7.62 (d, 2H, J=8 Hz)

Provenance & Evidence